Compound for organic electronic element, organic electrical element using compound, and electronic device comprising same

ABSTRACT

The objective of the present invention is to provide: a compound capable of ensuring high light-emitting efficiency and low driving voltage of an element, and increasing the lifespan thereof; an organic electrical element using compound; and an electronic device comprising the same.

TECHNICAL FIELD

The present invention relates to a compound for an organic electronicelement, an organic electronic element using the same, and an electronicdevice comprising the same.

BACKGROUND ART

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy of an organicmaterial using an organic material. An organic electronic elementutilizing the organic light emitting phenomenon usually has a structureincluding an anode, a cathode, and an organic material layer interposedtherebetween. In many cases, the organic material layer may have amultilayered structure including multiple layers made of differentmaterials in order to improve the efficiency and stability of an organicelectronic element, and for example, may include a hole injection layer,a hole transport layer, a light emitting layer, an electron transportlayer, an electron injection layer, or the like.

A material used as an organic material layer in an organic electronicelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, and the like according to its function.

Further, the light emitting material may be divided into a highmolecular weight type and a low molecular weight type according to itsmolecular weight, and may also be divided into a fluorescent materialderived from electronic excited singlet states and a phosphorescentmaterial derived from electronic excited triplet states according to itslight emitting mechanism. Further, the light emitting material may bedivided into blue, green, and red light emitting materials, and yellowand orange light emitting materials required for better natural colorreproduction according to its light emitting color.

When only one material is used as a light emitting material, there occurproblems of shift of a maximum luminescence wavelength to a longerwavelength due to intermolecular interactions and lowering of theefficiency of a corresponding element due to the deterioration in colorpurity or a reduction in luminous efficiency. On account of this, ahost/dopant system may be used as the light emitting material in orderto enhance the color purity and increase the luminous efficiency throughenergy transfer. This is based on the principle that if a small amountof dopant having a smaller energy band gap than a host forming a lightemitting layer is mixed in the light emitting layer, then excitonsgenerated in the light emitting layer are transported to the dopant,thus emitting light with high efficiency. With regard to this, since thewavelength of the host is shifted to the wavelength band of the dopant,light having a desired wavelength can be obtained according the type ofthe dopant.

Currently, the power consumption is required more and more as the sizeof display becomes larger and larger in the portable display market.Therefore, the power consumption is a very important factor in theportable display with a limited power source of the battery, andefficiency and lifetime issue also is solved.

Efficiency, lifetime, driving voltage, and the like are correlated witheach other. For example, if efficiency is increased, then drivingvoltage is relatively lowered, and the crystallization of an organicmaterial due to Joule heating generated during operation is reduced asdriving voltage is lowered, as a result of which lifetime shows atendency to increase. However, efficiency cannot be maximized only bysimply improving the organic material layer. This is because longlifetime and high efficiency can be simultaneously achieved when anoptimal combination of energy levels and T1 values, inherent materialproperties (mobility, interfacial properties, etc.), and the like amongthe respective layers included in the organic material layer is given.

That is, in order to allow the organic electronic element tosufficiently exhibit excellent characteristics, most of all, materialsconstituting an organic material layer in the element, for examples, ahole injection material, a hole transport material, a light emittingmaterial, an electron transport material, an electron injectionmaterial, and the like need to be supported by stable and efficientmaterials, but the development of stable and efficient materials for theorganic material layer for an organic electronic element is notsufficiently achieved. Therefore, the development of new materials iscontinuously required, and especially, the development of an electrontransport material and a light emitting material is urgently required.

Polycyclic compounds containing heteroatoms are very different from eachother with respect to characteristics resulting from the materialstructure, and thus are applied, as OLED materials, to various layers.

Especially, such compounds are different from each other with band gaps(HOMO, LUMO), electric characteristics, chemical characteristics,physical properties, and the like, and therefore, the applicationthereof to various OLED layers has been developed (application to HTL orphosphorescent host: U.S. Pat. No. 8,334,058, KR 1108398; andapplication to ETL: KR 0813385, KR 0765078). Recently, the developmentof OLED materials with respect to the kind, number, and position ofheteroatoms of pentacyclic compounds have been actively developed (KR1418146, KR 0938796, KR 2011-0043439, KR2012-0140557, KR 2013-0071547,JP 2010-230312, etc.)

DETAILED DESCRIPTION OF THE INVENTION Technical Problem

In order to solve the above-mentioned problems occurring in the priorart, an object of the present invention is to provide a compound capableof achieving high luminous efficiency, a low driving voltage, and animproved lifetime of an element, an organic electronic element using thesame, and an electronic device comprising the same.

The present company has been developing hepta-cyclic compound-relatedmaterials using the characteristics of the polycyclic compounds since2009 (KR 1108512, U.S. Ser. No. 13/390,043). However, the hepta-cycliccompounds have a relatively low lifetime in spite of favorableefficiency, and thus the application thereof to current OLED panels isvery difficult. Therefore, the present invention has a structure withseven rings, which is the same as in KR 1108512, but materials withhigh-efficiency and long-lifetime have been developed by varying thefused position constituting the penta-cyclic compounds and the kind andarrangement of heteroatoms.

Technical Solution

In accordance with an aspect of the present invention, there is provideda compound represented by the following formula.

In another aspect of the present invention, there are provided anorganic electronic element using the compound represented by the aboveformula, and an electronic device comprising the same.

Advantageous Effects

The use of the compound according to the present invention can achievehigh luminous efficiency and a low driving voltage of an element andsignificantly improving an improved lifetime of an element.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates an example of an organic light emitting diodeaccording to the present invention.

MODE FOR CARRYING OUT THE INVENTION

Hereinafter, some embodiments of the present invention will be describedin detail with reference to the accompanying illustrative drawings

In designation of reference numerals to components in respectivedrawings, it should be noted that the same elements would be designatedby the same reference numerals although they are shown in differentdrawings. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b), or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order, orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen” as used hereinincludes fluorine (F), bromine (Br), chlorine (Cl), and iodine (I).

Unless otherwise stated, the term “alkyl” or “alkyl group” as usedherein has a single bond of 1 to 60 carbon atoms, and means aliphaticfunctional radicals including a linear alkyl group, a branched chainalkyl group, a cycloalkyl group (alicyclic), or an alkyl groupsubstituted with a cycloalkyl.

Unless otherwise stated, the term “haloalkyl group” or “halogen alkylgroup” as used herein means an alkyl group substituted with halogen.

The term “heteroalkyl group” as used herein means an alkyl group ofwhich at least one of carbon atoms is substituted with a hetero atom.

Unless otherwise stated, the term “alkenyl” or “alkynyl” as used hereinhas, but not limited to, double or triple bonds of 2 to 60 carbon atoms,and includes a linear alkyl group, or a branched chain alkyl group.

Unless otherwise stated, the term “cycloalkyl” as used herein means, butnot limited to, alkyl forming a ring having 3 to 60 carbon atoms.

The term “alkoxyl group”, “alkoxy group” or “alkyloxy group” as usedherein means an alkyl group to which oxygen radical is attached, but notlimited to, and, unless otherwise stated, has 1 to 60 carbon atoms.

The term “alkenoxyl group”, “alkenoxy group”, “alkenyloxyl group”, or“alkenyloxy group” as used herein means an alkenyl group to which oxygenradical is attached, but not limited to, and, unless otherwise stated,has 2 to 60 carbon atoms.

The term “aryloxyl group” or “aryloxy group” as used herein means anaryl group to which oxygen radical is attached to, but not limited to,and has 6 to 60 carbon atoms.

Unless otherwise stated, the terms “aryl group” and “arylene group” eachhave 6 to 60 carbon atoms, but not limited thereto. The aryl group orarylene group herein means a monocyclic or polycyclic aromatic group,and includes an aromatic ring that is formed in conjunction with anadjacent substituent linked thereto or participating in the reaction.Examples of the aryl group may include a phenyl group, a biphenylylgroup, a terphenylyl group, a naphthyl group, an anthracenyl group, afluorene group, a spirofluorene group, and a spirobifluorene group.

The prefix “aryl” or “ar” means a radical substituted with an arylgroup. For example, an arylalkyl group may be an alkyl group substitutedwith an aryl group, and an arylalkenyl group may be an alkenyl groupsubstituted with an aryl group, and a radical substituted with an arylgroup has a number of carbon atoms defined as herein.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxygroup means an alkoxy group substituted with an aryl group, analkoxylcarbonyl group means a carbonyl group substituted with an alkoxylgroup, and an arylcarbonylalkenyl group also means an alkenyl groupsubstituted with an arylcarbonyl group, wherein the arylcarbonyl groupmay be a carbonyl group substituted with an aryl group.

Unless otherwise stated, the term “heteroalkyl” as used herein meansalkyl containing one or more heteroatoms.

Unless otherwise stated, the term “heteroaryl group” or “heteroarylenegroup” as used herein means, but not limited to, an aryl or arylenegroup having 2 to 60 carbon atoms and containing one or moreheteroatoms, includes at least one of monocyclic and polycyclic rings,and may also be formed in conjunction with an adjacent group.

Unless otherwise stated, the term “heterocyclic group” as used hereincontains one or more heteroatoms, has 2 to 60 carbon atoms, includes atleast one of homocyclic and heterocyclic rings, and may also be formedin conjunction with an adjacent group.

Unless otherwise stated, the term “heteroatom” as used herein representsN, O, S, P, or Si.

In addition, the “heterocyclic group” also may include a ring containingSO2 instead of carbon forming the ring. For examples, the “heterocyclicgroup” includes the following compound.

Unless otherwise stated, the term “aliphatic” as used herein means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring” as used herein means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring” means an aliphatic ring having3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, ahetero ring having 2 to 60 carbon atoms, or a fused ring formed by thecombination of them, and includes a saturated or unsaturated ring.

Hetero compounds or hetero radicals other than the above-mentionedhetero compounds each contain, but not limited to, one or moreheteroatoms.

Unless otherwise stated, the term “carbonyl” as used herein isrepresented by —COR′, wherein R′ may be hydrogen, an alkyl having 1 to20 carbon atoms, an aryl having 6 to 30 carbon atoms, a cycloalkylhaving 3 to 30 carbon atoms, an alkenyl having 2 to 20 carbon atoms, analkynyl having 2 to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “ether” as used herein is representedby —R—O—R′, wherein R′ may be hydrogen, an alkyl having 1 to 20 carbonatoms, an aryl having 6 to 30 carbon atoms, a cycloalkyl having 3 to 30carbon atoms, an alkenyl having 2 to 20 carbon atoms, an alkynyl having2 to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “substituted or unsubstituted” as usedherein means that substitution is carried out by at least onesubstituent selected from the group consisting of, but not limited to,deuterium, halogen, an amino group, a nitrile group, a nitro group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylamine group, aC₁-C₂₀ alkylthio group, a C₆-C₂₀ arylthio group, a C₂-C₂₀ alkenyl group,a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, a C₆-C₆₀ aryl group,a C₆-C₂₀ aryl group substituted by deuterium, a C₈-C₂₀ arylalkenylgroup, a silane group, a boron group, a germanium group, and a C₅-C₂₀heterocyclic group.

Otherwise specified, the formulas used in the present invention aredefined as in the index definition of the substituent of the followingFormula.

Wherein, when a is an integer of zero, the substituent R¹ is absent,when a is an integer of 1, the sole R¹ is linked to any one of thecarbon atoms constituting the benzene ring, when a is an integer of 2 or3, the substituent R¹'s may be the same and different, and are linked tothe benzene ring as follows. When a is an integer of 4 to 6, thesubstituents R¹'s may be the same and different, and are linked to thebenzene ring in a similar manner to that when a is an integer of 2 or 3,hydrogen atoms linked to carbon constituents of the benzene ring beingnot represented as usual.

FIG. 1 illustrates an organic electronic element according to anembodiment of the present invention.

Referring to FIG. 1, an organic electronic element 100 according to anembodiment of the present invention includes a first electrode 120formed on a substrate 110, a second electrode 180, and an organicmaterial layer between the first electrode 120 and the second electrode180, which contains the compound of the present invention. Here, thefirst electrode 120 may be an anode (positive electrode), and the secondelectrode 180 may be a cathode (negative electrode). In the case of aninverted organic electronic element, the first electrode may be acathode, and the second electrode may be an anode.

The organic material layer includes a hole injection layer 130, a holetransport layer 140, a light emitting layer 150, an electron transportlayer 160, and an electron injection layer 170 formed in sequence on thefirst electrode 120. Here, the layers included in the organic materiallayer, except the light emitting layer 150, may not be formed. Theorganic material layer may further include a hole blocking layer, anelectron blocking layer, an auxiliary light emitting layer 151, a bufferlayer 141, etc., and the electron transport layer 160 and the like mayserve as the hole blocking layer.

Although not shown, the organic electronic element according to anembodiment of the present invention may further include a protectivelayer or a light efficiency improving layer (capping layer) formed on atleast one of the sides the first and second electrodes, which is a sideopposite to the organic material layer.

The compound of the present invention employed in the organic materiallayer may be used as a host material, a dopant material, or a lightefficiency layer material in the hole injection layer 130, the holetransport layer 140, the electron transport layer 160, the electroninjection layer 170, the auxiliary light emitting layer 151, or thelight emitting layer 150. Preferably, the compound of the presentinvention may be used for the hole transport layer 140 and the auxiliarylight emitting layer 151.

Since depending on the type and position of a substituent to beattached, a band gap, electrical properties, interfacial properties, andthe like may vary even in the same core, it is very important what thetypes of core and a combination of substituent attached to the core are.Specially, long lifetime and high efficiency can be simultaneouslyachieved when an optimal combination of energy levels and T1 values,inherent material properties (mobility, interfacial properties, etc.),and the like among the respective layers included in the organicmaterial layer is given.

Accordingly, in the present invention, energy levels and T1 values andinherent material properties (mobility, interfacial properties, etc.),and the like among the respective layers included in the organicmaterial layer are optimized by forming a light emitting layer using thecompound represented by formula 1, and thus the lifetime and efficiencyof the organic electronic element can be improved at the same time.

An organic light emitting diode according to an embodiment of thepresent invention may be manufactured using a physical vapor deposition(PVD) method. For example, the organic electronic element may bemanufactured by depositing a metal, a metal oxide having conducive, oran alloy thereof, on the substrate to form the anode 120, forming theorganic material layer including the hole injection layer 130, the holetransport layer 140, the auxiliar light emitting layer 151, the lightemitting layer 150, the electron transport layer 160, and the electroninjection layer 170 thereon, and then depositing a material, which canbe used as the cathode 180, thereon.

Also, the organic material layer may be manufactured in such a mannerthat a smaller number of layers are formed using various polymermaterials by a soluble process or solvent process, for example, spincoating, dip coating, doctor blading, screen printing, inkjet printing,or thermal transfer, instead of deposition. Since the organic materiallayer according to the present invention may be formed in various ways,the scope of protection of the present invention is not limited by amethod of forming the organic material layer.

According to used materials, the organic electronic element according toan embodiment of the present invention may be of a top emission type, abottom emission type, or a dual emission typo.

A WOLED (White Organic Light Emitting Device) readily allows for theformation of ultra-high definition images, and is of excellentprocessability as well as enjoying the advantage of being produced usingconventional color filter technologies for LCDs. In this regard, variousstructures for WOLEDs, used as back light units, have been, in the mostpart, suggested and patented. Representative among the structures are aparallel side-by-side arrangement of R (Red), G (Green), B (Blue)light-emitting units, a vertical stack arrangement of RGB light-emittingunits, and a color conversion material (CCM) structure in whichelectroluminescence from a blue (B) organic light emitting layer, andphotoluminescence from an inorganic luminescent using theelectroluminescence are combined. The present invention is applicable tothese WOLEDs.

Further, the organic electronic element according to an embodiment ofthe present invention may be any one of an organic light emitting diode(OLED), an organic solar cell, an organic photo conductor (OPC), anorganic transistor (organic TFT), and an element for monochromatic orwhite illumination.

Another embodiment of the present invention provides an electronicdevice including a display device, which includes the above describedorganic electronic element, and a control unit for controlling thedisplay device. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, a compound according to an aspect of the present inventionwill be described.

The compound according to an aspect of the present invention isrepresented by Formula 1 below.

In Formula 1,

Ar¹ and Ar² each may be independently selected from the group consistingof a C₆-C₆₀ aryl group, a fluorenyl group, a fused ring group of aC₃-C₆₀ aliphatic group and a C₆-C₆₀ aromatic group, a C₂-C₆₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P, a C₁-C₅₀ alkyl group, and —N(R′)(R″).

Here, R′ and R″ each may be independently selected from the groupconsisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P, and a C₁-C₅₀ alkyl group.

L¹ and L² each may be selected from the group consisting of a singlebond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀ bivalentheterocyclic group containing at least one heteroatom of O, N, S, Si,and P, a fused ring group of a C₃-C₆₀ bivalent aliphatic group and aC₆-C₆₀ bivalent aromatic group, and a bivalent aliphatic hydrocarbongroup. Here, each of them (excluding the single bond) may be substitutedwith at least one substituent selected from the group consisting ofdeuterium, a nitro group, a nitrile group, a halogen group, a C₁-C₂₀alkyl group, a C₆-C₂₀ aryl group, a C₂-C₂₀ heterocyclic group, a C₁-C₂₀alkoxy group, and an amino group.

X¹ to X⁸ each are independently CR¹ or N.

R¹ may be selected from the group consisting of hydrogen, deuterium,halogen, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclicgroup containing at least one heteroatom of O, N, S, Si, and P, a fusedring group of a C₆-C₆₀ aromatic group and a C₃-C₆₀ aliphatic group, aC₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₁-C₃₀ alkoxy group, and aC₆-C₃₀ aryloxy group.

Alternatively, in the presence of a plurality of R¹'s, the plurality ofR¹'s may be different from or the same as each other and adjacent R¹'smay be linked to each other to form at least one ring (provided that R¹forming no ring is the same as defined in i) above). Here, R¹ forming noring may be the same as defined in above. The ring formed herein may bea C₃-C₆₀ aliphatic ring or a C₆-C₆₀ aromatic ring, a C₂-C₆₀ heterocyclicring, a C₃-C₆₀ alicyclic ring, or a fused ring formed of a combinationthereof, and may be a saturated or unsaturated ring as well as amonocyclic or polycyclic ring.

For example, when Ar¹, Ar², R′, R″, L¹, L², and R¹ are an aryl group oran arylene group, Ar¹, Ar², R′, r″, L¹, L², and R¹ each areindependently a phenyl group or phenylene group, a biphenyl group orbiphenyl group, a terphenyl group or terphenylene group, a naphthylgroup or naphthylene group, or a phenanthryl group or phenanthrylenegroup.

Ring A is a C₆-C₂₀ aromatic group condensed with two adjacent rings(thiophene and pyrrole). Here, the C₆-C₂₀ aromatic group of ring A maybe substituted with at least one group selected from the groupconsisting of deuterium, halogen, a C₆-C₆₀ aryl group, a fluorenylgroup, a C₂-C₆₀ heterocyclic group containing at least one heteroatom ofO, N, S, Si, and P, a halogen group, a C₁-C₅₀ alkyl group, a fused ringgroup of a C₆-C₆₀ aromatic group and a C₃-C₆₀ aliphatic group, a C₂-C₂₀alkenyl group, a C₁-C₃₀ alkoxy group, and a C₆-C₃₀ aryloxy group. In thepresence of a plurality of substituents, the plurality of substituentsmay be different from or the same as each other and adjacentsubstituents may be linked to each other to form at least one ring. Thering formed herein may be a C₃-C₆₀ aliphatic ring or a C₆-C₆₀ aromaticring, a C₂-C₆₀ heterocyclic ring, a C₃-C₆₀ alicyclic ring, or a fusedring formed of a combination thereof, and may be a saturated orunsaturated ring as well as a monocyclic or polycyclic ring.

Here, the C₆-C₂₀ aromatic group of ring A may be benzene, naphthalene,or phenanthrene, but is not limited thereto.

Specifically, ring A in Formula 1 above may be represented by one of theformulas A1 to A6 below.

In A1 to A6, *'s are binding positions at which any one side of each ofrings (thiophene and pyrrole) adjacent to ring A is shared andcondensed.

Here, 1 is an integer of 0 to 2, and m is an integer of 0 to 4.

R² and R² may be selected from the group consisting of deuterium,halogen, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclicgroup containing at least one heteroatom of O, N, S, Si, and P, ahalogen group, a C₁˜C₅₀ alkyl group, a fused ring group of a C₆-C₆₀aromatic group and a C₃-C₆₀ aliphatic group, a C₂-C₂₀ alkenyl group, aC₁-C₃₀ alkoxy group, and a C₆-C₃₀ aryloxy group.

Alternatively, in the presence of a plurality of R²'s and R³'s, theplurality of R²'s or R³'s are different from or the same as each otherand adjacent R²'s or R³'s may be linked to each other to form at leastone ring. Here, R² and R³ forming no ring each may be the same asdefined above. The ring formed herein may be a C₃-C₆₀ aliphatic ring ora C₆-C₆₀ aromatic ring, a C₂-C₆₀ hetero ring, a C₃-C₆₀ alicyclic ring,or a fused ring formed of a combination thereof, and may be a saturatedor unsaturated ring as well as a monocyclic or polycyclic ring.

Specifically, the compound represented by Formula 1 above may berepresented by one of the formulas below.

In Formula 2 to 5,

X¹ to X⁸, Ar¹, Ar², L¹, and L² each may be the same as defined inFormula 1 above.

Here, m is an integer of 0 to 2.

R⁴ may be selected from the group consisting of deuterium, halogen, aC₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom of O, N, S, Si, and P, a halogengroup, a C₁-C₅₀ alkyl group, a fused ring group of a C₆-C₆₀ aromaticgroup and a C₃-C₆₀ aliphatic group, a C₂-C₂₀ alkenyl group, a C₁-C₃₀alkoxy group, and a C₆-C₃₀ aryloxy group.

Alternatively, in the presence of a plurality of R⁴'s, the plurality ofR⁴'s each may be different from or the same as each other and adjacentR²'s may be linked to each other to form at least one ring. Here, R⁴forming no ring each may be the same as defined above. The ring formedherein may be a C₃-C₆₀ aliphatic ring group or a C₆-C₆₀ aromatic ring, aC₂-C₆₀ heterocyclic ring, a C₃-C₆₀ alicyclic group, or a fused ringformed of a combination thereof, and may be a saturated or unsaturatedring as well as a monocyclic or polycyclic ring.

In formulas 1 to 5, the aryl group, fluorenyl group, heterocyclic group,fused ring group, alkyl group, alkenyl group, alkoxy group, and aryloxygroup each may be substituted with at least one substituent selectedfrom the group consisting of deuterium, halogen, a silane group, asiloxane group, a boron group, a germanium group, a cyano group, a nitrogroup, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkylgroup, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ arylgroup, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenylgroup, a C₂-C₂₀ heterocyclic group, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀arylalkyl group, a C₈-C₂₀ arylalkenyl group, and —N(R^(a))(R^(b)).

R^(a) and R^(b) each may be independently selected from the groupconsisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P, and a C₁-C₅₀ alkyl group.

Here, the aryl group may be an aryl group having 6-60 carbon atoms,preferably 6-40 carbon atoms, and more preferably 6-30 carbon atoms;

the heterocyclic group may be a heterocyclic group having 2-60 carbonatoms, preferably 2-30 carbon atoms, and more preferably 2-20 carbonatoms; and

the alkyl group may be an alkyl group having 1-50 carbon atoms,preferably 1-30 carbon atoms, more preferably 1-20 carbon atoms, andespecially preferably 1-10 carbon atoms.

Specifically, the compound represented by Formula 1 above may berepresented by one of the formulas below.

In Formula 6 to 9,

X¹ to X⁸, Ar¹, Ar², L¹, and L² may be the same as X¹ to X⁸, Ar¹, Ar²,L¹, and L² defined in Formula 1 above.

More specifically, the compounds represented by Formulas 1 to 9 may beone of the following compounds.

In another embodiment, the present invention provides a compound for anorganic electronic element, represented by Formula 1.

In still another embodiment, the present invention provides an organicelectronic element containing the compound represented by Formula 1.

Here, the organic electronic element may include: a first electrode; asecond electrode; and an organic material layer positioned between thefirst electrode and the second electrode, wherein the organic materiallayer may contain a compound represented by Formula 1, and the compoundrepresented by Formula 1 may be contained in at least one of a holeinjection layer, a hole transport layer, an auxiliary light emittinglayer, a light emitting layer, an electron transport layer, and anelectron injection layer of an organic material layer. Especially, thecompound represented by Formula 1 may be contained in the light emittinglayer.

That is, the compound represented by Formula 1 may be used as a materialfor a hole injection layer, a hole transport layer, an auxiliary lightemitting layer, a light emitting layer, an electron transport layer, oran electron injection layer. Especially, the compound represented byFormula 1 may be used as a material for the light emitting layer. Thepresent invention provides, specifically, an organic electronic elementincluding the organic material layer containing one of the compoundsrepresented by Formulas 2 to 9, and more specifically, an organicelectronic element including the organic material layer containing thecompound represented by the above individual Formula (P-1 to P-171).

In still another embodiment, the present invention provides an organicelectronic element, in which the compound is contained alone, two ormore different kinds of the compounds are contained as a combination, orthe compound is contained together with other compounds as a combinationof two or more in at least one of the hole injection layer, the holetransport layer, the auxiliary light emitting layer, the light emittinglayer, the electron transport layer, and the electron injection layer ofthe organic material layer. In other words, the compounds correspondingto Formulas 1 to 9 may be contained alone, a mixture of two or morekinds of compounds of Formulas 1 to 9 may be contained, or a mixture ofthe compound of claims 1 to 5 and a compound not corresponding to thepresent invention may be contained in each of the layers. Here, thecompounds that do not correspond to the present invention may be asingle compound or two or more kinds of compounds. Here, when thecompound is contained together with other compounds as a combination oftwo or more kinds of compounds, the other compounds may be a compoundthat is already known for each organic material layer, or a compound tobe developed in the future. Here, the compounds contained in the organicmaterial layer may be composed of only the same kind of compounds, or amixture of two or more kinds of different compounds represented byFormula 1.

In still another embodiment of the present invention, the presentinvention provides an organic electronic element further including alight efficiency improvement layer, which is formed on at least one ofone side of one surface of the first electrode, which is opposite to theorganic material layer, and one side of one surface of the secondelectrode, which is opposite to the organic material layer.

Hereinafter, synthesis examples of the compound represented by Formula 1and manufacturing examples of the organic electronic element accordingto the present invention will be described in detail by way of example.However, the following examples are only for illustrative purposes andare not intended to limit the scope of the invention.

Synthesis Examples

The compounds (final products) represented by Formula 1 according to thepresent invention are synthesized by a reaction of Sub 1 and Sub 2 asshown in Reaction Scheme 1 below, but are not limited thereto.

(X¹ to X⁸, Ar¹, Ar², L¹, L², and A each are the same as defined inFormula 1 above)

I. Synthesis Example of Sub 1

Sub 1 in Reaction Scheme 1 above may be synthesized by a reactionpathway of Reaction Scheme 2, but is not limited thereto.

Synthesis examples of specific compounds pertaining to Sub 1 are asfollows.

Synthesis of Sub 1-24

(1) Synthesis of Sub 1-II-24

In a round-bottom flask, Sub 1-I-24 (160 g, 151.9 mmol) was added, andthen (2-nitrophenyl)boronic acid (86.1 g, 515.9 mmol), Pd(PPh₃)₄ (17.9g, 15.5 mmol), NaOH (61.9 g, 1548 mmol), THF (2270 ml), and water (1134ml) were added. Thereafter, the mixture was heated under reflux at80-90□. Upon completion of the reaction, the reaction product wasdiluted with distilled water at room temperature, followed by extractionwith methylene chloride and water. The organic layer was dried overMgSO₄ and concentrated, and then the compound thus formed was subjectedto silica gel column chromatography and recrystallization to give aproduct 152.6 g (yield: 77%).

(2) Synthesis of Sub 1-III-24

Sub 1-II-24 (151 g, 393.97 mmol) obtained in the above synthesis wasdissolved in o-dichlorobenzene (1572 ml) in a round bottom flask, andthen triphenylphosphine (309.2 g, 1179 mmol) was added, followed bystirring at 200□. Upon completion of the reaction, o-dichlorobenzene wasremoved through distillation, followed by extraction with CH₂Cl₂ andwater. The organic layer was dried over MgSO₄ and concentrated, and thenthe compound thus formed was subjected to silica gel columnchromatography and recrystallization to give a product 59.5 g (yield:43%).

(3) Synthesis of Sub 1-IV-24

Sub 1-III-24 (59 g, 167.5 mmol) was dissolved in nitrobenzene (838 ml)in a round bottom flask, and then 2-iodonaphthalene (46.8 g, 184.2mmol), Na₂SO₄ (23.8 g, 167.5 mmol), K₂CO₃ (23.1 g, 167.5 mmol), and Cu(3.2 g, 50.2 mmol) were added, followed by stirring at 200□. Uponcompletion of the reaction, nitrobenzene was removed throughdistillation, followed by extraction with CH₂Cl₂ and water. The organiclayer was dried over MgSO₄ and concentrated, and then the compound thusformed was subjected to silica gel column chromatography andrecrystallization to give a product 41.7 g (yield: 52%).

(4) Synthesis of Sub 1-V-24

In a round-bottom flask, Sub 1-IV-24 (40 g, 83.6 mmol) was added, andthen (2-nitrophenyl)boronic acid (14 g, 83.6 mmol), Pd(PPh₃)₄ (2.9 g,2.5 mmol), NaOH (10 g, 251 mmol), THF (368 ml), and water (184 ml) wereadded. Thereafter, the mixture was heated under reflux at 80-90□. Uponcompletion of the reaction, the reaction product was diluted withdistilled water at room temperature, followed by extraction withmethylene chloride and water. The organic layer was dried over MgSO₄ andconcentrated, and then the compound thus formed was subjected to silicagel column chromatography and recrystallization to give a product 34 g(yield: 78%).

(5) Synthesis of Sub 1-24

Sub 1-V-24 (28 g, 53.8 mmol) obtained in the above synthesis wasdissolved in o-dichlorobenzene (215 ml) in a round bottom flask, andthen triphenylphosphine (42.3 g, 161.4 mmol) was added, followed bystirring at 200□. Upon completion of the reaction, o-dichlorobenzene wasremoved through distillation, followed by extraction with CH₂Cl₂ andwater. The organic layer was dried over MgSO₄ and concentrated, and thenthe compound thus formed compound was subjected to silica gel columnchromatography and recrystallization to give a product 16.6 g (yield:63%).

2. Synthesis of Sub 1-36

(1) Synthesis of Sub 1-II-36

The synthesis method for Sub 1-II-24 was employed using Sub 1-I-36 (241g, 518.1 mmol), (2-nitrophenyl)boronic acid (86.5 g, 518.1 mmol),Pd(PPh₃)₄ (18 g, 15.5 mmol), NaOH (62.2 g, 1554 mmol), THF (2280 ml),and water (1140 ml) to give a product 188.4 g (yield: 79%).

(2) Synthesis of Sub 1-III-36

The synthesis method for Sub 1-III-24 was employed using Sub 1-II-36(187 g, 406.2 mmol), o-dichlorobenzene (1645 ml), and triphenylphosphine(319.6 g, 1218.7 mmol) to give a product 71.3 g (yield: 41%).

(3) Synthesis of Sub 1-IV-36

The synthesis method for Sub 1-IV-24 was employed using Sub 1-III-36(70.5 g, 164.6 mmol), nitrobenzene (823 ml), 2-iodo-1,1′-biphenyl (50.7g, 181 mmol), Na₂SO₄ (23.4 g, 164.6 mmol), K₂CO₃ (22.7 g, 164.6 mmol),and Cu (3.1 g, 49.4 mmol) to give a product 48.6 g (yield: 49%).

(4) Synthesis of Sub 1-V-36

The synthesis method for Sub 1-V-24 was employed using Sub 1-IV-36 (46g, 79.2 mmol), (2-nitrophenyl)boronic acid (13.2 g, 79.2 mmol),Pd(PPh₃)₄ (2.7 g, 2.4 mmol), NaOH (9.5 g, 238 mmol), THF (349 ml), andwater (174 ml) to give a product 35.5 g (yield: 72%).

(5) Synthesis of Sub 1-36

The synthesis method for Sub 1-24 was employed using Sub 1-V-36 (33 g,53 mmol) obtained from the synthesis above, o-dichlorobenzene (212 ml),and triphenylphosphine (41.7 g, 159 mmol) to give a product 16.4 g(yield: 60%).

3. Synthesis of Sub 1-59

(1) Synthesis of Sub 1-II-59

The synthesis method for Sub 1-II-24 was employed using Sub 1-I-59(357.5 g, 918.9 mmol), (2-nitropyridin-3-yl)boronic acid (154.3 g, 918.9mmol), Pd(PPh₃)₄ (31.9 g, 27.6 mmol), NaOH (110.3 g, 2757 mmol), THF(4043 ml), and water (2021 ml) to give a product 215.9 g (yield: 61%).

(2) Synthesis of Sub 1-III-59

The synthesis method for Sub 1-III-34 was employed using Sub 1-II-59(215.5 g, 559.4 mmol), o-dichlorobenzene (2237 ml), andtriphenylphosphine (440.2 g, 1678.2 mmol) to give a product 84.97 g(yield: 43%).

(3) Synthesis of Sub 1-IV-59

The synthesis method for Sub 1-IV-24 was employed using Sub 1-III-59(84.6 g, 239.5 mmol), nitrobenzene (1200 ml), 2-iodo-1,1′-biphenyl (73.8g, 263.4 mmol), Na₂SO₄ (34 g, 239.5 mmol), K₂CO₃ (33.1 g, 239.5 mmol),Cu (4.6 g, 71.8 mmol) to give a product 50.8 (yield: 42%).

(4) Synthesis of Sub 1-V-59

The synthesis method for Sub 1-V-24 was employed using Sub 1-IV-59 (50g, 98.9 mmol), (5-(naphthalen-2-yl)-2-nitrophenyl)boronic acid (29 g,98.9 mmol), Pd(PPh₃)₄ (3.4 g, 2.97 mmol), NaOH (11.9 g, 297 mmol), THF(435 ml), and water (218 ml) to give a product 41.3 g (yield: 62%).

(5) Synthesis of Sub 1-59

The synthesis method for Sub 1-24 was employed using Sub 1-V-59 (40 g,59.4 mmol) obtained from the synthesis above, o-dichlorobenzene (237ml), and triphenylphosphine (46.7 g, 178 mmol) to give a product 16 g(yield: 42%).

4. Synthesis of Sub 1-71

(1) Synthesis of Sub 1-II-71

The synthesis method for Sub 1-II-24 was employed using Sub 1-I-71 (308g, 701.4 mmol), (2-nitrophenyl)boronic acid (117.1 g, 701.4 mmol),Pd(PPh₃)₄ (24.3 g, 21 mmol), NaOH (84.2 g, 2104 mmol), THF (3086 ml),and water (1543 ml) to give a product 219.3 g (yield: 72%).

(2) Synthesis of Sub 1-III-71

The synthesis method for Sub 1-III-34 was employed using Sub 1-II-71(220 g, 506.5 mmol), o-dichlorobenzene (2,026 ml), andtriphenylphosphine (398.6 g, 1519.7 mmol) to give a product 87.6 g(yield: 43%).

(3) Synthesis of Sub 1-IV-71

The synthesis method for Sub 1-IV-24 was employed using Sub 1-III-71 (79g, 196.4 mmol), nitrobenzene (982 ml), 4-iodo-1,1′-biphenyl (60.5 g, 216mmol), Na₂SO₄ (27.9 g, 196.4 mmol), K₂CO₃ (27.1 g, 196.4 mmol), and Cu(3.7 g, 58.9 mmol) to give a product 49 g (yield: 45%).

(4) Synthesis of Sub 1-V-71

The synthesis method for Sub 1-V-24 was employed using Sub 1-IV-71 (48g, 86.6 mmol), (2-nitrophenyl)boronic acid (14.5 g, 86.6 mmol),Pd(PPh₃)₄ (3 g, 2.6 mmol), NaOH (10.4 g, 259.7 mmol), THF (381 ml), andwater (190 ml) to give a product 35.1 g (yield: 68%).

(5) Synthesis of Sub 1-71

The synthesis method for Sub 1-24 was employed using Sub 1-V-71 (31 g,52 mmol) obtained from the synthesis above, o-dichlorobenzene (208 ml),and triphenylphosphine (40.9 g, 156 mmol) to give a product 13.2 g(yield: 45%).

5. Synthesis of Sub 1-63

(1) Synthesis of Sub 1-II-63

The synthesis method for Sub 1-II-24 was employed using Sub 1-I-63 (251g, 645.2 mmol), (2-nitrophenyl)boronic acid (107.7 g, 645.2 mmol),Pd(PPh₃)₄ (22.4 g, 19.4 mmol), NaOH (77.4 g, 1935 mmol), THF (2839 ml),and water (1419 ml) to give a product 188.4 g (yield: 76%).

(2) Synthesis of Sub 1-III-63

The synthesis method for Sub 1-III-24 was employed using Sub 1-II-63(105 g, 273.3 mmol), o-dichlorobenzene (1093 ml), and triphenylphosphine(215 g, 819.8 mmol) to give a product 40.4 g (yield: 42%).

(3) Synthesis of Sub 1-IV-63

The synthesis method for Sub 1-IV-24 was employed using Sub 1-III-63 (38g, 107.9 mmol), nitrobenzene (540 ml), iodobenzene (24.2 g, 118.7 mmol),Na₂SO₄ (15.3 g, 107.9 mmol), K₂CO₃ (14.9 g, 107.9 mmol), and Cu (2.1 g,32.4 mmol) to give a product 31.9 g (yield: 69%).

(4) Synthesis of Sub 1-V-63

The synthesis method for Sub 1-V-24 was employed using Sub 1-IV-63 (31g, 72.4 mmol), (2-nitrophenyl)boronic acid (12.1 g, 72.4 mmol),Pd(PPh₃)₄ (2.5 g, 2.2 mmol), NaOH (8.7 g, 217.1 mmol), THF (318 ml), and(159 ml) to give a product 26.9 g (yield: 79%).

(5) Synthesis of Sub 1-63

The synthesis method for Sub 1-24 was employed using Sub 1-V-63 (26 g,55 mmol) obtained from the synthesis above, o-dichlorobenzene (221 ml),and triphenylphosphine (43.5 g, 166 mmol) to give a product 16.5 g(yield: 68%).

6. Synthesis of Sub 1-107

(1) Synthesis of Sub 1-II-107

The synthesis method for Sub 1-II-24 was employed using Sub 1-I-107 (275g, 626.3 mmol), (2-nitrophenyl)boronic acid (104.5 g, 626.3 mmol),Pd(PPh₃)₄ (21.7 g, 18.8 mmol), NaOH (75.2 g, 1879 mmol), THF (2756 ml),and water (1378 ml) to give a product 190.4 g (yield: 70%).

(2) Synthesis of Sub 1-III-107

The synthesis method for Sub 1-III-24 was employed using Sub 1-II-107(189.5 g, 436.3 mmol), o-dichlorobenzene (1745 ml), andtriphenylphosphine (343.3 g, 1309 mmol) to give a product 82.5 g (yield:41%).

(3) Synthesis of Sub 1-IV-107

The synthesis method for Sub 1-IV-24 was employed using Sub 1-III-107(82.2 g, 204.3 mmol), nitrobenzene (1022 ml),5′-bromo-1,1′:3′,1″-terphenyl (69.5 g, 224.8 mmol), Na₂SO₄ (29 g, 204.3mmol), K₂CO₃ (28.2 g, 204.3 mmol), and Cu (3.9 g, 61.3 mmol) to give aproduct 60.6 g (yield: 47%).

(4) Synthesis of Sub 1-V-107

The synthesis method for Sub 1-V-24 was employed using Sub 1-IV-107 (60g, 95.1 mmol), (4-nitro-[1,1′-biphenyl]-3-yl)boronic acid (23.1 g, 95.1mmol), Pd(PPh₃)₄ (3.3 g, 2.9 mmol), NaOH (11.4 g, 285.4 mmol), THF (419ml), and water (209 ml) to give a product 36.3 g (yield: 51%).

(5) Synthesis of Sub 1-107

The synthesis method for Sub 1-24 was employed using Sub 1-V-107 (35 g,46.7 mmol) obtained from the synthesis above, o-dichlorobenzene (187ml), and triphenylphosphine (36.8 g, 140 mmol) to give a product 16.4 g(yield: 49%).

Meanwhile, the compounds pertaining to Sub 1 may be compounds below, butare not limited thereto. Table 1 below shows FD-MS values of thecompounds pertaining to Sub 1.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1-1 m/z = 438.12 (C₃₀H₁₈N₂S =438.54) Sub 1-2 m/z = 488.13 (C₃₄H₂₀N₂S = 488.60) Sub 1-3 m/z = 514.15(C₃₆H₂₂N₂S = 514.64) Sub 1-4 m/z = 514.15 (C₃₆H₂₂N₂S = 514.64) Sub 1-5m/z = 590.18 (C₄₂H₂₆N₂S = 590.73) Sub 1-6 m/z = 554.18 (C₃₉H₂₆N₂S =554.70) Sub 1-7 m/z = 544.11 (C₃₆H₂₀N₂S₂ = 544.69) Sub 1-8 m/z = 544.11(C₃₆H₂₀N₂S₂ = 544.69) Sub 1-9 m/z = 593.17 (C₃₉H₂₃N₅S = 593.70) Sub 1-10m/z = 603.23 (C₃₉H₁₃D₁₀N₅S = 603.76) Sub 1-11 m/z = 566.16 (C₃₈H₂₂N₄S =566.67) Sub 1-12 m/z = 566.16 (C₃₈H₂₂N₄S = 566.67) Sub 1-13 m/z = 718.22(C₅₀H₃₀N₄S = 718.87) Sub 1-14 m/z = 656.17 (C₄₄H₂₄N₄OS = 656.75) Sub1-15 m/z = 622.13 (C₄₀H₂₂N₄S₂ = 622.76) Sub 1-16 m/z = 774.19(C₅₂H₃₀N₄S₂ = 774.95) Sub 1-17 m/z = 620.14 (C₄₂H₂₄N₂S₂ = 620.78) Sub1-18 m/z = 635.24 (C₄₅H₂₅D₅N₂S = 635.83) Sub 1-19 m/z = 690.21(C₅₀H₃₀N₂S = 690.85) Sub 1-20 m/z = 565.16 (C₃₉H₂₃N₃S = 565.69) Sub 1-21m/z = 567.15 (C₃₇H₂₁N₅S = 567.66) Sub 1-22 m/z = 438.12 (C₃₀H₁₈N₂S =438.54) Sub 1-23 m/z = 488.13 (C₃₄H₂₀N₂S = 488.60) Sub 1-24 m/z = 488.13(C₃₄H₂₀N₂S = 488.60) Sub 1-25 m/z = 514.15 (C₃₆H₂₂N₂S = 514.64) Sub 1-26m/z = 514.15 (C₃₆H₂₂N₂S = 514.64) Sub 1-27 m/z = 514.16 (C₃₆H₂₂N₂S =514.64) Sub 1-28 m/z = 564.17 (C₄₀H₂₄N₂S = 564.70) Sub 1-29 m/z = 519.18(C₃₆H₁₇D₅N₂S = 519.67) Sub 1-30 m/z = 544.11 (C₃₆H₂₀N₂S₂ = 544.69) Sub1-31 m/z = 515.15 (C₃₅H₂₁N₃S = 515.63) Sub 1-32 m/z = 488.13 (C₃₄H₂₀N₂S= 488.60) Sub 1-33 m/z = 691.21 (C₄₉H₂₉N₃S = 691.84) Sub 1-34 m/z =440.11 (C₂₈H₁₆N₄S = 440.52) Sub 1-35 m/z = 438.12 (C₃₀H₁₈N₂S = 438.54)Sub 1-36 m/z = 590.18 (C₄₂H₂₆N₂S = 590.73) Sub 1-37 m/z = 514.15(C₃₆H₂₂N₂S = 514.64) Sub 1-38 m/z = 514.15 (C₃₆H₂₂N₂S = 514.64) Sub 1-39m/z = 538.15 (C₃₈H₂₂N₂S = 538.66) Sub 1-40 m/z = 443.15 (C₃₀H₁₃D₅N₂S =443.57) Sub 1-41 m/z = 515.15 (C₃₉H₂₁N₃S = 515.63) Sub 1-42 m/z = 514.15(C₃₆H₂₂N₂S = 514.64) Sub 1-43 m/z = 514.15 (C₃₆H₂₂N₂S = 514.64) Sub 1-44m/z = 640.20 (C₄₆H₂₈N₂S = 640.79) Sub 1-45 m/z = 590.18 (C₄₂H₂₆N₂S =590.73) Sub 1-46 m/z = 540.14 (C₃₆H₂₀N₄S = 540.64) Sub 1-47 m/z = 438.12(C₃₀H₁₈N₂S = 438.54) Sub 1-48 m/z = 488.13 (C₃₄H₂₀N₂S = 488.60) Sub 1-49m/z = 488.13 (C₃₄H₂₀N₂S = 488.60) Sub 1-50 m/z = 514.15 (C₃₆H₂₂N₂S =514.64) Sub 1-51 m/z = 640.20 (C₄₆H₂₈N₂S = 640.79) Sub 1-52 m/z = 514.15(C₃₆H₂₂N₂S = 514.64) Sub 1-53 m/z = 538.15 (C₃₈H₂₂N₂S = 538.66) Sub 1-54m/z = 590.18 (C₄₂H₂₆N₂S = 590.73) Sub 1-55 m/z = 528.13 (C₃₆H₂₀N₂OS =528.62) Sub 1-56 m/z = 514.15 (C₃₆H₂₂N₂S = 514.64) Sub 1-57 m/z = 588.17(C₄₂H₂₁N₂S = 588.72) Sub 1-58 m/z = 545.10 (C₃₅H₁₉N₃S₂ = 545.68) Sub1-59 m/z = 641.19 (C₄₅H₂₇N₃S = 641.78) Sub 1-60 m/z = 538.15 (C₃₈H₂₂N₂S= 538.66) Sub 1-61 m/z = 514.15 (C₃₆H₂₂N₂S = 514.64) Sub 1-62 m/z =514.15 (C₃₆H₂₂N₂S = 514.64) Sub 1-63 m/z = 438.12 (C₃₀H₁₈N₂S = 438.54)Sub 1-64 m/z = 564.17 (C₄₀H₂₄N₂S = 564.70) Sub 1-65 m/z = 528.13(C₃₆H₂₀N₂OS = 528.62) Sub 1-66 m/z = 488.13 (C₃₄H₂₀N₂S = 488.60) Sub1-67 m/z = 488.13 (C₃₄H₂₀N₂S = 488.60) Sub 1-68 m/z = 438.12 (C₃₀H₁₈N₂S= 438.54) Sub 1-69 m/z = 488.13 (C₃₄H₂₀N₂S = 488.60) Sub 1-70 m/z =488.13 (C₃₄H₂₀N₂S = 488.60) Sub 1-71 m/z = 514.15 (C₃₆H₂₂N₂S = 514.64)Sub 1-72 m/z = 514.15 (C₃₆H₂₂N₂S = 514.64) Sub 1-73 m/z = 514.15(C₃₆H₂₂N₂S = 514.64) Sub 1-74 m/z = 640.20 (C₄₆H₂₈N₂S = 640.79) Sub 1-75m/z = 538.15 (C₃₀H₂₂N₂S = 538.66) Sub 1-76 m/z = 745.23 (C₅₁H₃₁N₅S =745.89) Sub 1-77 m/z = 439.11 (C₂₉H₁₇N₃S = 439.53) Sub 1-78 m/z = 488.13(C₃₄H₂₀N₂S = 488.60) Sub 1-79 m/z = 564.17 (C₄₀H₂₄N₂S = 564.70) Sub 1-80m/z = 564.17 (C₄₀H₂₄N₂S = 564.70) Sub 1-81 m/z = 588.17 (C₄₂H₂₄N₂S =588.72) Sub 1-82 m/z = 616.17 (C₄₂H₂₄N₄S = 616.73) Sub 1-83 m/z = 614.18(C₄₄H₂₆N₂S = 614.76) Sub 1-84 m/z = 488.13 (C₃₄H₂₀N₂S = 488.60) Sub 1-85m/z = 538.15 (C₃₈H₂₂N₂S = 538.66) Sub 1-86 m/z = 538.15 (C₃₈H₂₂N₂S =538.66) Sub 1-87 m/z = 564.17 (C₄₀H₂₄N₂S = 564.70) Sub 1-88 m/z = 614.18(C₄₄H₂₆N₂S = 614.76) Sub 1-89 m/z = 538.15 (C₃₈H₂₂N₂S = 538.66) Sub 1-90m/z = 514.15 (C₃₆H₂₂N₂S = 514.64) Sub 1-91 m/z = 516.17 (C₃₆H₂₄N₂S =516.65) Sub 1-92 m/z = 538.15 (C₃₈H₂₂N₂S = 538.66) Sub 1-93 m/z = 593.20(C₄₂H₁₉D₅N₂S = 593.75) Sub 1-94 m/z = 488.13 (C₃₄H₂₀N₂S = 488.60) Sub1-95 m/z = 538.15 (C₃₈H₂₂N₂S = 538.66) Sub 1-96 m/z = 564.17 (C₄₀H₂₄N₂S= 564.70) Sub 1-97 m/z = 564.17 (C₄₀H₂₄N₂S = 564.70) Sub 1-98 m/z =493.17 (C₃₄H₁₅D₅N₂S = 493.63) Sub 1-99 m/z = 643.18 (C₄₃H₂₅N₅S = 643.76)Sub 1-100 m/z = 642.19 (C₄₄H₂₆N₄S = 642.77) Sub 1-101 m/z = 489.13(C₃₃H₁₉N₃S = 489.59) Sub 1-102 m/z = 538.15 (C₃₈H₂₂N₂S = 538.66) Sub1-103 m/z = 539.15 (C₃₇H₂₁N₃S = 539.65) Sub 1-104 m/z = 640.20(C₄₈H₂₈N₂S = 640.79) Sub 1-105 m/z = 564.17 (C₄₀H₂₄N₂S = 564.70) Sub1-106 m/z = 564.17 (C₄₀H₂₄N₂S = 564.70) Sub 1-107 m/z = 716.23(C₅₂H₃₂N₂S = 716.89)

II. Synthesis of Sub 2

Sub 2 of Reaction Scheme 1 above may be synthesized by a reactionpathway of Reaction Scheme 9, but is not limited thereto.

Synthesis of Sub 2-18

After phenylboronic acid pinacol ester (26 g, 90.4 mmol) was dissolvedin THF (398 ml), 3,7-dibromo-1,5-naphthyridine (18 g, 90.4 mmol),Pd(PPh₃)₄ (3.1 g, 2.7 mmol), K₂CO₃ (37.5 g, 271 mmol), and water (200ml), followed by stirring at 90□. Upon completion of the reaction, thereaction product was extracted with ether and water. The organic layerwas dried over MgSO₄ and concentrated, and then the resulting organicmaterial was subjected to silica gel column chromatography andrecrystallization to give a product 12.4 g (yield: 48%).

2. Synthesis of Sub 2-21

The synthesis method for Sub 2-18 was employed using Phenylboronic acidpinacol ester (31.2 g, 152.7 mmol), THF (336 ml),2,4,6-trichloropyrimidine (14 g, 76 mmol), Pd(PPh₃)₄ (5.3 g, 4.58 mmol),K₂CO₃ (63.3 g, 458 mmol), and (168 ml) to give a product 13.2 g (yield:65%).

3. Synthesis of Sub 2-33

The synthesis method for Sub 2-18 was employed using phenylboronic acidpinacol ester (24.6 g, 120.5 mmol), THF (531 ml),2,4-dichloroquinazoline (24 g, 120.5 mmol), Pd(PPh₃)₄ (4.2 g, 3.62mmol), K₂CO₃ (50 g, 361.7 mmol), and water (265.3 ml) to give a product13.93 g (yield: 48%).

4. Synthesis of Sub 2-53

The synthesis method for Sub 2-18 was employed using phenylboronic acidpinacol ester (21.6 g, 106 mmol), THF (466 ml),2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine (27 g, 106 mmol),Pd(PPh₃)₄ (3.7 g, 3.18 mmol), K₂CO₃ (43.9 g, 317.5 mmol), and (233 ml)to give a product 13.8 g (yield: 44%).

Meanwhile, the compounds pertaining to Sub 2 may be compounds below, butare not limited thereto. Table 2 below shows FD-MS values of thecompounds pertaining to Sub 2.

TABLE 2 Compound FD-MS Compound FD-MS Sub 2-1 m/z = 155.96 (C₆H₅Br =157.01) Sub 2-2 m/z = 205.97 (C₁₀H₇Br = 207.07) Sub 2-3 m/z = 205.97(C₁₀H₇Br = 207.07) Sub 2-4 m/z = 231.99 (C₁₂H₉Br = 233.10) Sub 2-5 m/z =231.99 (C₁₂H₉Br = 233.10) Sub 2-6 m/z = 308.02 (C₁₈H₁₃Br = 309.20) Sub2-7 m/z = 261.95 (C₁₂H₇BrS = 263.15) Sub 2-8 m/z = 321.02 (C₁₈H₁₂BrN =322.20) Sub 2-9 m/z = 322.01 (C₁₇H₁₁BrN₂ = 323.19) Sub 2-10 m/z = 206.97(C₉H₆BrN = 208.05) Sub 2-11 m/z = 232.98 (C₁₁H₈BrN = 234.09) Sub 2-12m/z = 283.00 (C₁₅H₁₀BrN = 284.15) Sub 2-13 m/z = 233.98 (C₁₀H₇BrN₂ =235.08) Sub 2-14 m/z = 310.01 (C₁₆H₁₁BrN₂ = 311.18) Sub 2-15 m/z =310.01 (C₁₆H₁₁BrN₂ = 311.18) Sub 2-16 m/z = 266.06 (C₁₆H₁₁ClN₂ = 266.72)Sub 2-17 m/z = 316.08 (C₂₀H₁₃ClN₂ = 316.78) Sub 2-18 m/z = 283.99(C₁₄H₉BrN₂ = 285.14) Sub 2-19 m/z = 233.98 (C₁₀H₇BrN₂ = 235.08) Sub 2-20m/z = 266.06 (C₁₆H₁₁ClN₂ = 266.72) Sub 2-21 m/z = 267.06 (C₁₆H₁₁ClN₂ =267.71) Sub 2-22 m/z = 277.12 (C₁₅D₁₀ClN₃ = 277.77) Sub 2-23 m/z =367.09 (C₂₃H₁₄ClN₃ = 367.83) Sub 2-24 m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.27)Sub 2-25 m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.27) Sub 2-26 m/z = 387.04(C₂₁H₁₄BrN₃ = 388.26) Sub 2-27 m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.27) Sub2-28 m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.27) Sub 2-29 m/z = 387.04(C₂₁H₁₄BrN₃ = 388.26) Sub 2-30 m/z = 462.07 (C₂₈H₁₉BrN₂ = 463.37) Sub2-31 m/z = 463.07 (C₂₇H₁₈BrN₃ = 464.36) Sub 2-32 m/z = 462.07(C₂₈H₁₉BrN₂ = 463.37) Sub 2-33 m/z = 240.05 (C₁₄H₉ClN₂ = 240.69) Sub2-34 m/z = 316.08 (C₂₀H₁₃ClN₂ = 316.78) Sub 2-35 m/z = 360.03(C₂₀H₁₃BrN₂ = 361.23) Sub 2-36 m/z = 436.06 (C₂₆H₁₇BrN₂ = 437.33) Sub2-37 m/z = 366.09 (C₂₄H₁₅ClN₂ = 366.84) Sub 2-38 m/z = 380.07(C₂₄H₃₃ClN₂O = 380.83) Sub 2-39 m/z = 340.08 (C₂₂H₁₃ClN₂ = 340.81) Sub2-40 m/z = 340.08 (C₂₂H₁₃ClN₂ = 340.81) Sub 2-41 m/z = 290.06(C₁₈H₁₁ClN₂ = 290.75) Sub 2-42 m/z = 340.08 (C₂₂H₁₃ClN₂ = 340.81) Sub2-43 m/z = 240.05 (C₁₄H₉ClN₂ = 240.69) Sub 2-44 m/z = 290.06 (C₁₈H₁₁ClN₂= 290.75) Sub 2-45 m/z = 316.08 (C₂₀H₁₃ClN₂ = 316.78) Sub 2-46 m/z =290.06 (C₁₈H₁₁ClN₂ = 290.75) Sub 2-47 m/z = 390.09 (C₂₆H₁₅ClN₂ = 390.86)Sub 2-48 m/z = 283.99 (C₃₄H₉BrN₂ = 285.14) Sub 2-49 m/z = 512.09(C₃₂H₂₁BrN₂ = 513.43) Sub 2-50 m/z = 283.99 (C₁₄H₉BrN₂ = 285.14) Sub2-51 m/z = 322.01 (C₁₇H₁₁BrN₂ = 323.19) Sub 2-52 m/z = 241.04 (C₁₃H₈ClN₃= 241.68) Sub 2-53 m/z = 296.02 (C₁₆H₉ClN₂S = 296.77) Sub 2-54 m/z =492.03 (C₂₈H₁₇BrN₂S = 493.42) Sub 2-55 m/z = 476.05 (C₂₈H₁₇BrN₂O =477.35) Sub 2-56 m/z = 280.04 (C₁₆H₉ClN₂O = 280.71) Sub 2-57 m/z =330.06 (C₂₀H₁₁ClN₂O = 330.77) Sub 2-58 m/z = 356.07 (C₂₂H₁₃ClN₂O =356.80)

III. Synthesis of Final Product

Sub 1 compound (1.1 eq.), Sub 2 compound (1 eq.), Pd₂(dba)₃ (0.05 eq.),P(t-Bu)₃ (0.1 eq.), NaOt-Bu (3 eq.), and toluene (10.5 mL/1 mmol) wereadded in a round-bottom flask, followed by a reaction at 100□. Uponcompletion of the reaction, the reaction product was extracted withether and water. The organic layer was dried over MgSO₄ andconcentrated, and then the resulting organic material was subjected tosilica gel column chromatography and recrystallization to give aproduct.

Synthesis of P-31

Sub 1-24 (14 g, 28.7 mmol), Sub 2-33 (7.6 g, 31.5 mmol), Pd₂(dba)₃ (1.3g, 1.4 mmol), P(t-Bu)₃ (0.6 g, 2.87 mmol), NaOt-Bu (8.3 g, 86 mmol), andtoluene (301 ml) were added in a round-bottom flask, followed by areaction at 100□. Upon completion of the reaction, the reaction productwas extracted with ether and water. The organic layer was dried overMgSO₄ and concentrated, and then the resulting organic material wassubjected to silica gel column chromatography and recrystallization togive a product 11 g (yield: 55%).

2. Synthesis of P-69

The synthesis method for P-31 was employed using Sub 1-36 (14 g, 23.7mmol), Sub 2-18 (7.4 g, 26 mmol), Pd₂(dba)₃ (1.1 g, 1.2 mmol), P(t-Bu)₃(0.5 g, 2.4 mmol), NaOt-Bu (6.8 g, 71 mmol), and toluene (250 ml) togive a product 10.9 g (yield: 58%).

3. Synthesis of P-91

The synthesis method for P-31 was employed using Sub 1-59 (15 g, 23.4mmol), Sub 2-3 (5.3 g, 25.7 mmol), Pd₂(dba)₃ (1.1 g, 1.17 mmol),P(t-Bu)₃ (0.5 g, 2.3 mmol), NaOt-Bu (6.7 g, 70 mmol), and toluene (245ml) to give a product 10.4 g (yield: 62%).

4. Synthesis of P-118

The synthesis method for P-31 was employed using Sub 1-79 (12 g, 21.3mmol), Sub 2-21 (6.3 g, 23.4 mmol), Pd₂(dba)₃ (1 g, 1.1 mmol), P(t-Bu)₃(0.4 g, 2.1 mmol), NaOt-Bu (6.1 g, 63.8 mmol), and toluene (223 ml) in around-bottom flask, to give a product 12.2 g (yield: 72%).

5. Synthesis of P-96

The synthesis method for P-31 was employed using Sub 1-63 (10 g, 22.8mmol), Sub 2-54 (12.4 g, 25.1 mmol), Pd₂(dba)₃ (1 g, 1.1 mmol), P(t-Bu)₃(0.5 g, 2.3 mmol), NaOt-Bu (6.6 g, 68.4 mmol), and toluene (240 ml) togive a product 14.2 g (yield: 73%).

6. Synthesis of P-152

The synthesis method for P-31 was employed using Sub 1-107 (14 g, 19.5mmol), Sub 2-10 (4.5 g, 21.5 mmol), Pd₂(dba)₃ (0.9 g, 0.98 mmol),P(t-Bu)₃ (0.4 g, 1.95 mmol), NaOt-Bu (5.6 g, 58.6 mmol), and toluene(205 ml) to give a product 10.55 g (yield: 64%).

TABLE 3 Compound FD-MS Compound FD-MS P-1 m/z = 564.17 (C₄₀H₂₄N₂S =564.70) P-2 m/z = 640.20 (C₄₆H₂₈N₂S = 640.79) P-3 m/z = 747.18(C₅₁H₂₉N₃S₂ = 747.93) P-4 m/z = 748.18 (C₅₀H₂₈N₄S₂ = 748.91) P-5 m/z =808.23 (C₅₆H₃₂N₄OS = 808.94) P-6 m/z = 900.24 (C₆₂H₃₆N₄S₂ = 901.11) P-7m/z = 668.20 (C₄₆H₂₈N₄S = 688.81) P-8 m/z = 668.20 (C₄₆H₂₈N₄S = 688.81)P-9 m/z = 755.29 (C₅₁H₂₁D₁₀N₅S = 755.95) P-10 m/z = 669.20 (C₄₅H₂₇N₅S =669.79) P-11 m/z = 744.23 (C₅₂H₃₂N₄S = 74 4.90) P-12 m/z = 745.23(C₅₁H₃₁N₅S = 745.89) P-13 m/z = 820.27 (C₅₈H₃₆N₄S = 821.00) P-14 m/z =784.27 (C₅₅H₃₆N₄S = 784.97) P-15 m/z = 820.27 (C₅₈H₃₆N₄S = 821.00) P-16m/z = 642.19 (C₄₄H₂₆N₄S = 642.77) P-17 m/z = 794.25 (C₅₆H₃₄N₄S = 794.96)P-18 m/z = 798.19 (C₅₄H₃₀N₄S₂ = 798.97) P-19 m/z = 718.22 (C₅₄H₃₀N₄S₂ =718.87) P-20 m/z = 718.22 (C₅₀H₃₀N₄S = 718.87) P-21 m/z = 794.25(C₅₆H₃₄N₄S = 794.96) P-22 m/z = 642.19 (C₄₄H₂₆N₄S = 642.77) P-23 m/z =840.31 (C₅₈H₃₂D₅N₅S = 841.04) P-24 m/z = 766.24 (C₅₆H₃₄N₂S = 766.95)P-25 m/z = 748.18 (C₅₀H₂₈N₄S₂ = 748.91) P-26 m/z = 807.25 (C₅₆H₃₃N₅S =807.96) P-27 m/z = 643.18 (C₄₃H₂₅N₅S = 643.76) P-28 m/z = 823.25(C₅₅H₃₃N₇S = 823.96) P-29 m/z = 614.18 (C₄₄H₂₆N₂S = 614.76) P-30 m/z =716.23 (C₅₂H₃₂N₂S = 716.89) P-31 m/z = 692.20 (C₄₈H₂₈N₄S = 692.83) P-32m/z = 692.20 (C₄₈H₂₈N₄S = 692.83) P-33 m/z = 870.28 (C₆₂H₃₈N₄S = 871.06)P-34 m/z = 668.20 (C₄₆H₂₈N₄S = 668.81) P-35 m/z = 718.22 (C₅₀H₃₀N₄S =718.87) P-36 m/z = 845.26 (C₅₉H₃₅N₅S = 846.01) P-37 m/z = 774.19(C₅₂H₃₀N₄S₂ = 774.95) P-38 m/z = 808.23 (C₅₆H₃₂N₄OS = 808.94) P-39 m/z =834.25 (C₅₈H₃₄N₄OS = 834.98) P-40 m/z = 729.28 (C₄₉H₁₉D₁₀N₅S = 729.91)P-41 m/z = 744.23 (C₅₂H₃₂N₄S = 744.90) P-42 m/z = 870.28 (C₆₂H₃₈N₄S =871.06) P-43 m/z = 718.22 (C₅₀H₃₀N₄S = 718.87) P-44 m/z = 673.23(C₄₆H₂₃D₅N₄S = 673.84) P-45 m/z = 824.21 (C₅₆H₃₂N₄S₂ = 825.01) P-46 m/z= 767.24 (C₅₅H₃₃N₃S = 767.94) P-47 m/z = 859.30 (C₆₂H₄₁N₃S = 860.07)P-48 m/z = 668.20 (C₄₆H₂₈N₄S = 668.81) P-49 m/z = 666.21 (C₄₈H₃₀N₂S =666.83) P-50 m/z = 671.24 (C₄₀H₂₅D₅N₂S = 671.86) P-51 m/z = 696.17(C₄₈H₂₈N₂S₂ = 696.88) P-52 m/z = 717.22 (C₅₁H₃₃N₃S = 717.88) P-53 m/z =768.23 (C₅₄H₃₂N₄S = 768.92) P-54 m/z = 668.20 (C₄₆H₂₈N₄S = 668.81) P-55m/z = 669.20 (C₄₅H₂₇N₅S = 669.79) P-56 m/z = 744.23 (C₅₂H₃₂N₄S = 744.90)P-57 m/z = 744.23 (C₅₂H₃₂N₄S = 000.00) P-58 m/z = 897.29 (C₆₃H₃₉N₅S =898.08) P-59 m/z = 668.20 (C₄₈H₂₈N₄S = 668.81) P-60 m/z = 748.18(C₅₀H₂₈N₄S₂ = 748.91) P-61 m/z = 682.18 (C₄₆H₂₆N₄OS = 682.79) P-62 m/z =718.22 (C₅₀H₃₀N₄S = 718.87) P-63 m/z = 858.25 (C₆₀H₃₄N₄OS = 859.00) P-64m/z = 818.25 (C₅₈H₃₄N₄S = 818.98) P-65 m/z = 794.25 (C₅₆H₃₄N₄S = 794.96)P-66 m/z = 719.2 (C₄₉H₂₉N₅S = 719.85) P-67 m/z = 768.23 (C₅₄H₃₂N₄S =768.92) P-68 m/z = 742.22 (C₅₂H₃₀N₄S = 742.89) P-69 m/z = 794.25(C₅₆H₃₄N₄S = 794.96) P-70 m/z = 755.24 (C₅₄H₃₃N₃S = 755.92) P-71 m/z =808.27 (C₅₁H₃₆N₄S = 808.99) P-72 m/z = 719.21 (C₄₉H₂₉N₅S = 719.85) P-73m/z = 716.23 (C₅₂H₃₂N₂S = 716.89) P-74 m/z = 664.20 (C₄₈H₂₈N₂S = 664.81)P-75 m/z = 758.21 (C₅₂H₃₀N₄OS = 758.89) P-76 m/z = 774.19 (C₅₂H₃₀N₄S₂ =774.95) P-77 m/z = 692.20 (C₄₈H₂₈N₄S = 692.83) P-78 m/z = 844.27(C₆₀H₃₆N₄S = 845.02) P-79 m/z = 742.22 (C₅₂H₃₀N₄S = 742.89) P-80 m/z =934.28 (C₆₆H₃₈N₄OS = 935.10) P-81 m/z = 718.22 (C₅₀H₃₀N₄S = 718.87) P-82m/z = 792.23 (C₅₆H₃₂N₄S = 792.95) P-83 m/z = 668.20 (C₄₆H₂₈N₄S = 668.81)P-84 m/z = 744.23 (C₅₂H₃₂N₄S = 744.90) P-85 m/z = 719.21 (C₄₉H₂₉N₅S =719.85) P-86 m/z = 744.23 (C₅₂H₃₂N₄S = 744.90) P-87 m/z = 744.23(C₅₂H₃₂N₄S = 744.90) P-88 m/z = 835.24 (C₅₇H₃₃N₅OS = 835.97) P-89 m/z =820.27 (C₅₈H₃₆N₄S = 821.00) P-90 m/z = 787.19 (C₅₂H₂₉N₅S₂ = 787.95) P-91m/z = 717.22 (C₅₁H₃₁N₃S = 717.88) P-92 m/z = 744.23 (C₅₂H₃₂N₄S = 744.90)P-93 m/z = 766.24 (C₅₆H₃₄N₂S = 766.95) P-94 m/z = 718.22 (C₅₀H₃₀N₄S =718.87) P-95 m/z = 768.23 (C₅₄H₃₂N₄S = 768.92) P-96 m/z = 850.22(C₃₈H₃₄N₄S₂ = 851.05) P-97 m/z = 794.25 (C₅₆H₃₄N₄S = 794.96) P-98 m/z =758.21 (C₅₂H₃₀N₄OS = 758.89) P-99 m/z = 719.21 (C₄₉H₂₉N₅S = 719.85)P-100 m/z = 732.20 (C₅₀H₂₈N₄OS = 732.85) P-101 m/z = 716.23 (C₅₂H₃₂N₂S =716.89) P-102 m/z = 842.28 (C₆₂H₃₈N₂S = 843.04) P-103 m/z = 742.22(C₅₂H₃₀N₄S = 742.89) P-104 m/z = 748.18 (C₅₀H₂₈N₄S₂ = 748.91) P-105 m/z= 850.22 (C₅₈H₃₄N₄S₂ = 851.05) P-106 m/z = 769.23 (C₅₃H₃₁N₅S = 769.91)P-107 m/z = 744.23 (C₅₂H₃₂N₄S = 744.90) P-108 m/z = 768.23 (C₅₄H₃₂N₄S =768.92) P-109 m/z = 821.26 (C₅₇H₃₅N₅S = 821.99) P 110 m/z = 823.24(C₅₆H₃₃N₅OS = 823.96) P-111 m/z = 746.25 (C₅₂H₃₄N₄S = 746.92) P-112 m/z= 716.23 (C₅₂H₃₂N₂S = 716.89) P-113 m/z = 842.28 (C₆₂H₃₈N₂S = 843.04)P-114 m/z = 742.22 (C₅₂H₃₀N₄S = 742.89) P-115 m/z = 868.27 (C₆₂H₃₆N₄S =869.04) P-116 m/z = 718.22 (C₅₀H₃₀N₄S = 718.87) P-117 m/z = 718.22(C₅₀H₃₀N₄S = 718.87) P-118 m/z = 795.25 (C₅₅H₃₃N₅S = 795.95) P-119 m/z =845.26 (C₅₈H₃₅N₅S = 846.01) P-120 m/z = 870.28 (C₆₂H₃₈N₄S = 871.06)P-121 m/z = 844.27 (C₆₀H₃₆N₄S = 845.02) P-122 m/z = 782.21 (C₅₄H₃₀N₄OS =782.91) P-123 m/z = 721.23 (C₅₀H₂₃D₅N₄S = 721.88) P-124 m/z = 740.23(C₅₄H₃₂N₂S = 740.91) P-125 m/z = 818.25 (C₅₉H₃₄N₄S = 818.98) P-126 m/z =818.25 (C₅₈H₃₄N₄S = 818.98) P-127 m/z = 795.25 (C₅₅H₃₃N₅S = 795.95)P-128 m/z = 844.27 (C₅₀H₃₆N₄S = 845.02) P-129 m/z = 845.26 (C₅₉H₃₅N₅S =846.01) P-130 m/z = 692.20 (C₄₈H₂₈N₄S = 692.83) P-131 m/z = 792.23(C₅₆H₃₂N₄S = 792.95) P-132 m/z = 848.21 (C₅₈H₃₂N₄S₂ = 849.03) P-133 m/z= 664.20 (C₄₈H₂₈N₂S = 664.81) P-134 m/z = 894.28 (C₅₄H₃₈N₄S = 895.08)P-135 m/z = 844.27 (C₆₀H₃₆N₄S = 845.02) P-136 m/z = 808.23 (C₅₆H₃₂N₄OS =808.94) P-137 m/z = 838.19 (C₅₆H₃₀N₄OS₂ = 838.99) P-138 m/z = 795.25(C₅₅H₃₃N₅S = 795.95) P-139 m/z = 870.28 (C₆₂H₃₈N₄S = 871.06) P-140 m/z =795.25 (C₅₅H₃₃N₅S = 795.95) P-141 m/z = 888.31 (C₆₇H₃₂D₅N₅S = 889.09)P-142 m/z = 692.20 (C₄₈H₂₈N₄S = 692.83) P-143 m/z = 792.26 (C₅₈H₃₆N₂S =792.98) P-144 m/z = 721.16 (C₄₉H₂₇N₃S₂ = 721.89) P-145 m/z = 692.20(C₄₈H₂₈N₄S = 692.83) P-146 m/z = 792.23 (C₅₆H₃₂N₄S = 792.95) P-147 m/z =808.23 (C₅₆H₃₂N₄OS = 808.94) P-148 m/z = 692.20 (C₄₈H₂₈N₄S = 692.83)P-149 m/z = 946.31 (C₆₈H₄₂N₄S = 947.15) P-150 m/z = 920.30 (C₆₆H₄₀N₄S =921.12) P-151 m/z = 871.28 (C₆₁H₃₇N₅S = 872.04) P-152 m/z = 843.27(C₆₁H₃₇N₃S = 844.03) P-153 m/z = 890.23 (C₆₁H₃₇N₅S = 891.07) P-154 m/z =839.24 (C₆₁H₃₇N₅S = 840.06) P-155 m/z = 890.23 (C₆₁H₃₇N₅S = 891.07)P-156 m/z = 731.20 (C₆₁H₃₇N₅S = 731.86) P-157 m/z = 889.26 (C₆₁H₃₇N₅S =890.12) P-158 m/z = 938.24 (C₆₁H₃₇N₅S = 939.15) P-159 m/z = 887.30(C₆₁H₃₇N₅S = 888.08) P-160 m/z = 924.29 (C₆₅H₄₀N₄OS = 1002.19) P-161 m/z= 940.27 (C₆₅H₄₀N₄S₂ = 941.17) P-162 m/z = 964.23 (C₆₆H₃₆N₄OS₂ = 965.15)P-163 m/z = 822.26 (C₅₆H₃₄N₆S = 822.97) P-164 m/z = 823.25 (C₅₅H₃₃N₇S =823.96) P-165 m/z = 822.26 (C₅₆H₃₄N₆S = 822.97) P-165 m/z = 784.24(C₅₃H₃₂N₆S = 784.93) P-167 m/z = 746.23 (C₅₀H₃₀N₆S = 746.88) P-166 m/z =872.27 (C₆₀H₃₆N₆S = 873.03) P-169 m/z = 948.30 (C₆₆H₄₀N₆S = 949.13)P-170 m/z = 885.26 (C₆₁H₃₅N₅OS = 886.03) P-171 m/z = 695.19 (C₄₅H₂₅N₇S =695.79)

Although the exemplary synthesis examples of the present inventionrepresented by Formula 1 have been described above, the synthesisexamples are on the basis of a Suzuki cross-coupling reaction, aDiazotization-Thiocyanation reaction (Org. Biomol. Chem. 2011, 9, 6066),an MW (Microwave)-assisted cyclization reaction (Org. Biomol. Chem.2011, 9, 6066), a PPh3-mediated reductive cyclization reaction (J. Org.Chem. 2005, 70, 5014.), ab Ullmann reaction and a Buchwald-Hartwig crosscoupling reaction. A person skilled in the art could easily understandthat the above reactions proceed even though, besides the substituentsspecified in the specific synthesis examples, the other substituents(Ar¹, Ar², R¹, R², R³, L¹, L², and X¹ to X⁸) defined in Formula 1 arebound.

Manufacturing and Evaluation of Organic Electronic Element

[Example 1] Green Organic Light Emitting Diode (Phosphorescent Host)

An organic electronic light emitting diode was manufactured by anordinary method using the compound obtained through the synthesis as alight emitting host material for a light emitting layer. First, a filmofN¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine(hereinafter, abbreviated as “2-TNATA”) was vacuum-deposited with athickness of 60 nm on an ITO layer (anode) formed on a galas substrate.Then, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter,abbreviated as “NPD”) as a hole transport compound was vacuum-depositedwith a thickness of 60 nm on the film, to form a hole transport layer.Subsequently, a light emitting layer with a thickness of 30 nm wasdeposited on the auxiliary light emitting layer by doping, on the holetransport layer, compound P-4 of the present invention as a host andIr(ppy)₃ [tris(2-phenylpyridine)-iridium] as a dopant at a weight ratioof 95:5. Then,(1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as “BAlq”) was vacuum-deposited with athickness of 10 nm for a hole blocking layer, andtris(8-quinolinol)aluminum (hereinafter abbreviated as “Alq₃”) wasformed with a thickness of 40 for an electron injection layer.Thereafter, LiF as halogenated alkali metal was deposited with athickness of 0.2 nm, and subsequently Al was deposited with a thicknessof 150 nm, thereby using this Al/LiF as a negative electrode. In thisway, an organic electronic light emitting diode was manufactured.

[Example 2] to [Example 21] Green Organic Light Emitting Diode(Phosphorescent Host)

Organic light emitting diodes were manufactured by the same method as inExample 1 except that, instead of inventive compound P-4, the inventivecompounds shown in table 4 below were used as a host material for alight emitting layer.

[Comparative Examples 1] to [Comparative Example 5]

Organic light emitting diodes were manufactured by the same method as inExample 1 except that, instead of inventive compound P-4, comparativecompounds A to E were used as a host material for a light emittinglayer.

A forward bias DC voltage was applied to each of the organic lightemitting diodes manufactured in Examples I1 to 21 and ComparativeExamples 1 to 5 to measure electro-luminescent (EL) characteristicsthereof by PR-650 (Photoresearch). Also, the T95 lifetime was measuredby the lifetime measurement equipment (Mcscience) at referencebrightness of 5000 cd/m². The measurement results are shown in Table 4below.

TABLE 4 Current Density Brightness Efficiency CIE Compound Voltage(mA/cm2) (cd/m2) (cd/A) T (95) X Y Comparative Comparative 6.3 21.2 500023.6 68.5 0.33 0.62 Example (1) Compound A Comparative Comparative 6.224.2 5000 20.7 57.8 0.33 0.62 Example (2) Compound B ComparativeComparative 5.9 22.1 5000 22.6 62.2 0.33 0.61 Example (3) Compound CComparative Comparative 6 14.4 5000 31.8 94.1 0.33 0.61 Example (4)Compound D Comparative Comparative 5.7 10.8 5000 36.2 84.7 0.33 0.62Example (5) Compound E Example (1) Compound 5.2 10.6 5000 47.3 138.60.33 0.62 (P-4) Example (2) Compound 5.1 10.6 5000 47.0 140.7 0.33 0.62(P-5) Example (3) Compound 5.0 10.3 5000 47.9 143.6 0.33 0.62 (P-7)Example (4) Compound 5.1 10.0 5000 48.2 143.2 0.33 0.62 (P-8) Example(5) Compound 5.0 10.1 5000 49.6 144.9 0.33 0.62 (P-9) Example (6)Compound 5.0 10.4 5000 50.2 145.8 0.33 0.61 (P-10) Example (7) Compound5.1 11.0 5000 45.6 138.4 0.33 0.62 (P-11) Example (8) Compound 5.2 10.85000 46.3 140.1 0.33 0.61 (P-12) Example (9) Compound 5.1 11.1 5000 45.1140.9 0.33 0.61 (P-13) Example (10) Compound 5.2 10.5 5000 47.5 136.40.33 0.61 (P-15) Example (11) Compound 5.2 12.3 5000 40.8 125.6 0.330.61 (P-28) Example (12) Compound 5.1 10.8 5000 46.5 138.4 0.33 0.61(P-34) Example (13) Compound 5.2 10.7 5000 45.6 135.8 0.33 0.62 (P-35)Example (14) Compound 5.1 11.0 5000 46.9 139.4 0.33 0.61 (P-36) Example(15) Compound 5.3 11.6 5000 43.0 133.1 0.33 0.61 (P-37) Example (16)Compound 5.3 12.3 5000 40.8 127.4 0.33 0.61 (P-39) Example (17) Compound5.2 11.4 5000 43.8 132.8 0.33 0.61 (P-41) Example (18) Compound 5.1 11.75000 42.8 134.9 0.33 0.61 (P-42) Example (19) Compound 5.3 11.4 500044.1 128.9 0.33 0.61 (P-49) Example (20) Compound 5.1 10.2 5000 50.1146.3 0.33 0.61 (P-53) Example (21) Compound 5.2 10.1 5000 50.6 146.50.33 0.62 (P-54) Example (22) Compound 5.2 10.2 5000 50.2 144.3 0.330.62 (P-55) Example (23) Compound 5.2 11.0 5000 46.7 140.2 0.33 0.61(P-56) Example (24) Compound 5.2 10.9 5000 47.1 140.7 0.33 0.62 (P-57)Example (25) Compound 5.3 10.8 5000 47.6 137.6 0.33 0.61 (P-58) Example(26) Compound 5.2 10.7 5000 48.1 139.2 0.33 0.62 (P-60) Example (27)Compound 5.2 11.1 5000 46.3 137.3 0.33 0.62 (P-61) Example (28) Compound5.4 12.5 5000 39.9 117.6 0.33 0.62 (P-73) Example (29) Compound 5.1 11.85000 42.3 128.5 0.33 0.61 (P-75) Example (30) Compound 5.2 12.1 500041.3 126.7 0.33 0.62 (P-76) Example (31) Compound 5.2 11.5 5000 43.4130.2 0.33 0.61 (P-83) Example (32) Compound 5.1 11.3 5000 44.4 134.40.33 0.62 (P-84) Example (33) Compound 5.0 11.6 5000 43.2 134.7 0.330.62 (P-85) Example (34) Compound 5.1 12.1 5000 41.2 126.7 0.33 0.62(P-86) Example (35) Compound 5.3 11.8 5000 42.4 128.7 0.33 0.62 (P-87)Example (36) Compound 5.1 12.0 5000 41.5 123.1 0.33 0.62 (P-88) Example(37) Compound 5.5 12.4 5000 40.3 121.6 0.33 0.62 (P-90) Example (38)Compound 5.4 12.5 5000 40.0 107.9 0.33 0.61 (P-96) Example (39) Compound5.4 11.9 5000 42.1 124.7 0.33 0.61 (P-97) Example (40) Compound 5.5 12.75000 39.3 117.9 0.33 0.62 (P-98) Example (41) Compound 5.5 11.8 500042.2 127.4 0.33 0.61 (P-99) Example (42) Compound 5.4 12.9 5000 38.9114.4 0.33 0.62 (P-105) Example (43) Compound 5.5 12.7 5000 39.3 120.61.33 0.62 (P-106) Example (44) Compound 5.5 12.0 5000 41.6 132.9 0.330.62 (P-107) Example (45) Compound 5.5 13.0 5000 38.3 101.5 0.33 0.61(P-109)

As can be seen from the results of table 4 above, it was verified that,when comparing comparative compound B, C, D, and E, which arehepta-cyclic compound similar to the present inventive compounds, andcomparative compound A, which is generally widely used, comparativecompound E had the highest efficiency and comparative compound D had thelongest lifetime.

Especially, as a result of investigating the lifetimes of comparativecompounds B and C, it was verified that the hepta-cyclic compound showeda shortened lifetime when it contains fluorene, and furthermore,comparative compound B having two fluorenes showed a longer lifetimethan comparative compound C having one fluorene.

It was confirmed from table 4 that the present inventive compounds,which have a similar fused position to the core of compound D and have atype of N—S—N, similar to that of comparative compound E, showed thehigher efficiency and longer lifetime than comparative compounds D andE.

This indicates that, although the hepta-cyclic compounds have the sameN—S—N type heteroatoms therein, the compounds have varied lifetimesdepending on the fused position and may have varied efficiencycharacteristics depending on the kind and arrangement of heteroatomscontained therein.

Therefore, it is considered that the efficiency and lifetime of ahepta-cyclic compound is not easy to predict due to the difference inthe fused position and the differences in the kind and arrangement ofheteroatoms in the compound.

[Example 22] Red Organic Light Emitting Diode (Phosphorescent Host)

An organic electronic light emitting diode was manufactured by anordinary method using the compound obtained through the synthesis as alight emitting host material for a light emitting layer. First, a filmof 2-TNATA was vacuum-deposited on an ITO layer (anode) formed on agalas substrate to form a hole injection layer with a thickness of 60nm, and then, a film of NPD as a hole transport compound wasvacuum-deposited with a thickness of 60 nm on the hole injection layerto form a hole transport layer. Then, a light emitting layer with athickness of 30 nm was deposited on the hole transport layer by dopinginventive compound P-16 as a host material and (piq)₂Ir(acac) as adopant material at a weight ratio of 95:5. Then, BAlq wasvacuum-deposited with a thickness of 10 nm as a hole blocking layer, anda film of Alq₃ was formed with a thickness of 40 nm for an electrontransport layer. Thereafter, LiF as halogenated alkali metal wasdeposited to a thickness of 0.2 nm for an electron injection layer, andthen Al was deposited to a thickness of 150 nm and used as a cathode,and ultimately, an organic light emitting diode was manufactured.

[Example 23] to [Example 42] Red Organic Light Emitting Diode(Phosphorescent Host)

Organic light emitting diodes were manufactured by the same method as inExample 22 except that, instead of inventive compound P-16, theinventive compounds shown in table 5 below were used as a host materialfor a light emitting layer.

[Comparative Examples 6] to [Comparative Example 9]

Organic light emitting diode was manufactured by the same method as inExample 22 except that, instead of inventive compound P-16, comparativecompound A, D, F, or G was used as a host material for a light emittinglayer.

A forward bias DC voltage was applied to each of the organic lightemitting diodes manufactured in Examples 22 to 42 and ComparativeExamples 6 to 9 to measure electro-luminescent (EL) characteristicsthereof by PR-650 (Photoresearch). Also, the T95 lifetime was measuredby the lifetime measurement equipment (Mcscience) at referencebrightness of 2500 cd/m². The measurement results are shown in Table 5below.

TABLE 5 Current Density Brightness Efficiency CIE Compound Voltage(mA/cm2) (cd/m2) (cd/A) T (95) x Comparative Comparative 6.5 34.7 25007.2 60.3 0.66 0.32 Example (6) Compound A Comparative Comparative 6.729.4 2500 8.5 98.7 0.66 0.32 Example (7) Compound D ComparativeComparative 6.4 27.2 2500 9.2 57.2 0.66 0.33 Example (8) Compound FComparative Comparative 6.1 20.2 2500 12.4 87.4 0.66 0.33 Example (9)Compound G Example (46) Compound 5.9 17.1 2500 14.7 148.9 0.66 0.33(P-16) Example (47) Compound 6.0 18.0 2500 13.9 141.8 0.66 0.32 (P-19)Example (48) Compound 6.0 17.2 2500 14.5 146.2 0.66 0.32 (P-20) Example(49) Compound 5.9 18.0 2500 13.9 141.7 0.66 0.32 (P-21) Example (50)Compound 5.9 18.1 2500 13.8 142.8 0.66 0.32 (P-27) Example (51) Compound5.9 18.9 2500 13.2 144.1 0.66 0.33 (P-31) Example (52) Compound 6.1 18.92500 13.3 142.5 0.66 0.32 (P-32) Example (53) Compound 5.9 19.7 250012.7 139.5 0.66 0.33 (P-45) Example (54) Compound 5.9 16.7 2500 15.0150.0 0.66 0.33 (P-62) Example (55) Compound 5.9 20.5 2500 12.2 138.20.66 0.32 (P-63) Example (56) Compound 6.0 18.8 2500 13.3 143.7 0.660.32 (P-65) Example (57) Compound 5.8 16.8 2500 14.9 147.9 0.66 0.33(P-67) Example (58) Compound 6.0 19.3 2500 13.0 139.3 0.66 0.33 (P-77)Example (59) Compound 5.8 19.2 2500 13.0 140.5 0.66 0.32 (P-81) Example(60) Compound 6.1 20.5 2500 12.2 136.7 0.66 0.33 (P-94) Example (61)Compound 6.1 19.5 2500 12.8 135.7 0.66 0.32 (P-95) Example (62) Compound6.2 24.1 2500 10.4 126.6 0.66 0.33 (P-103) Example (63) Compound 6.124.1 2500 10.4 125.2 0.66 0.32 (P-104) Example (64) Compound 5.8 17.42500 14.4 151.2 0.66 0.33 (P-114) Example (65) Compound 5.8 16.7 250014.9 150.3 0.66 0.32 (P-115) Example (66) Compound 6.0 18.7 2500 13.4147.1 0.66 0.32 (P-130) Example (67) Compound 5.8 18.7 2500 13.4 146.90.66 0.32 (P-135) Example (68) Compound 5.9 19.3 2500 13.0 142.5 0.660.32 (P-145)

As can be seen from the results of table 5 above, it was verified that,when comparing comparative compound D, F, and G, which are hepta-cycliccompound similar to the present inventive compounds, and comparativecompound A, which is generally widely used, comparative compound G hadthe highest efficiency and comparative compound D had the longestlifetime.

Similarly, as a result of investigating the lifetime of comparativecompound F, it was verified that the hepta-cyclic compound showed ashortened lifetime when it contains fluorene, and furthermore, and itwas confirmed from table 5 that the present inventive compounds, whichhave a similar fused position to the core of compound compound D andhave a type of N—S—N, similar to that of comparative compound G, showedthe higher efficiency and longer lifetime than comparative compounds Dand G.

This indicates that, although the hepta-cyclic compounds have the sameN—S—N type heteroatoms therein, the compounds have varied lifetimesdepending on the fused position and may have varied efficiencycharacteristics depending on the kind and arrangement of heteroatomscontained therein.

Therefore, it is considered that the efficiency and lifetime of ahepta-cyclic compound is not easy to predict due to the difference inthe fused position and the differences in the kind and arrangement ofheteroatoms in the compound.

In addition, the characteristics of elements have been described in viewof a light emitting layer with reference to the foregoing evaluationresults of the manufacture of elements, but the materials used for alight emitting layer may be ordinarily used alone or in a mixture withother materials, for the foregoing organic material layer for an organicelectronic element, such as an electron transport layer, an electroninjection layer, a hole injection layer, a hole transport layer, and anauxiliary light emitting layer. Therefore, for the foregoing reasons,the compounds of the present invention may be used alone or in a mixturewith other materials, for the other layers for an organic materiallayer, excluding the light emitting layer, for example, an electrontransport layer, an electron injection layer, a hole injection layer, ahole transport layer, and an auxiliary light emitting layer.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, a person skilled in the art willappreciate that various modifications, additions, and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

EXPLANATION OF NUMERICAL REFERENCES

-   -   100: organic electronic element    -   110: substrate    -   120: first electrode    -   130: hole injection layer    -   140: hole transport layer    -   141: buffer layer    -   150: light emitting layer    -   151: auxiliary light emitting layer    -   160: electron transport layer    -   170: electron injection layer    -   180: second electrode

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims priority under 35 U.S.C. §119(a) onKorean Patent Application No. 10-2014-0114083, filed on 29 Aug. 2014,the disclosure of which is incorporated herein by reference. Inaddition, this patent application claims priorities in countries otherthan U.S., with the same reason based on the Korean Patent Application,the entire contents of which are incorporated herein by reference.

1. A compound represented by Formula 1:

wherein in Formula 1, Ar¹ and Ar² each are independently selected fromthe group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a fusedring group of a C₃-C₆₀ aliphatic group and a C₆-C₆₀ aromatic group, aC₂-C₆₀ heterocyclic group containing at least one heteroatom of O, N, S,Si, and P, a C₁-C₅₀ alkyl group, and —N(R′)(R″); R′ and R″ each areindependently selected from the group consisting of a C₆-C₆₀ aryl group,a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom of O, N, S, Si, and P, and a C₁-C₅₀ alkyl group; L¹ and L²each are selected from the group consisting of a single bond, a C₆-C₆₀arylene group, a fluorenylene group, a C₂-C₆₀ bivalent heterocyclicgroup containing at least one heteroatom of O, N, S, Si, and P, a fusedring group of a C₃-C₆₀ bivalent aliphatic group and a C₆-C₆₀ bivalentaromatic group, and a bivalent aliphatic hydrocarbon group, each ofwhich (excluding the single bond) may be substituted with at least onesubstituent selected from the group consisting of deuterium, a nitrogroup, a nitrile group, a halogen group, a C₁-C₂₀ alkyl group, a C₆-C₂₀aryl group, a C₂-C₂₀ heterocyclic group, a C₁-C₂₀ alkoxy group, and anamino group; X¹ to X⁸ each are independently CR¹ or N; i) R¹ is selectedfrom the group consisting of hydrogen, deuterium, halogen, a C₆-C₆₀ arylgroup, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing atleast one heteroatom of O, N, S, Si, and P, a fused ring group of aC₆-C₆₀ aromatic group and a C₃-C₆₀ aliphatic group, a C₁-C₅₀ alkylgroup, a C₂-C₂₀ alkenyl group, a C₁-C₃₀ alkoxy group, and a C₆-C₃₀aryloxy group, or ii) in the presence of a plurality of R¹'s, theplurality of R¹'s are different from or the same as each other andadjacent R¹'s may be linked to each other to form at least one ring(provided that R¹ forming no ring is the same as defined in i) above);ring A is a C₆-C₂₀ aromatic group condensed with two adjacent rings(thiophene and pyrrole); the C₆-C₂₀ aromatic group of ring A may besubstituted with at least one group selected from the group consistingof deuterium, halogen, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P, a halogen group, a C₁-C₅₀ alkyl group, a fused ring group of aC₆-C₆₀ aromatic group and a C₃-C₆₀ aliphatic group, a C₂-C₂₀ alkenylgroup, a C₁-C₃₀ alkoxy group, and a C₆-C₃₀ aryloxy group; and, in thepresence of a plurality of substituents, the plurality of substituentsare different from or the same as each other and adjacent substituentsmay be linked to each other to form at least one ring; the aryl group,fluorenyl group, heterocyclic group, fused ring group, alkyl group,alkenyl group, alkoxy group, and aryloxy group each may be substitutedwith at least one substituent selected from the group consisting ofdeuterium, halogen, a silane group, a siloxane group, a boron group, agermanium group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group,a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, aC₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl groupsubstituted with deuterium, a fluorenyl group, a C₂-C₂₀ heterocyclicgroup, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group, a C₈-C₂₀arylalkenyl group, and —N(R^(a))(R^(b)); and R^(a) and R^(b) each areindependently selected from the group consisting of a C₆-C₆₀ aryl group,a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom of O, N, S, Si, and P, and a C₁-C₅₀ alkyl group.
 2. Thecompound of claim 1, wherein ring A is represented by one of theformulas below:

wherein in A1 to A6, *'s are binding positions at which any one side ofeach of rings (thiophene and pyrrole) adjacent to ring A is shared andcondensed; 1 is an integer of 0 to 2, and m is an integer of 0 to 4; R²and R² are i) selected from the group consisting of deuterium, halogen,a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom of O, N, S, Si, and P, a fused ringgroup of a C₆-C₆₀ aromatic group and a C₃-C₆₀ aliphatic group, a C₂-C₂₀alkenyl group, a C₁-C₃₀ alkoxy group, and a C₆-C₃₀ aryloxy group, or ii)in the presence of a plurality of R²'s and R³'s, the plurality of R²'sor R³'s are different from or the same as each other and adjacent R²'sor R³'s may be linked to each other to form at least one ring (providedthat R² and R³ forming no ring are the same as defined in i) above); andthe aryl group, fluorenyl group, heterocyclic group, fused ring group,alkyl group, alkenyl group, alkoxy group, and aryloxy group each may besubstituted with at least one substituent selected from the groupconsisting of deuterium, halogen, a silane group, a siloxane group, aboron group, a germanium group, a cyano group, a nitro group, a C₁-C₂₀alkylthio group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀heterocyclic group, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group,and a C₈-C₂₀ arylalkenyl group.
 3. The compound of claim 1, wherein thecompound is represented by one of the formulas below:

wherein in Formula 2 to 5; X¹ to X⁸, Ar¹, Ar², L¹ and L² each are thesame as defined in Formula 1 above; m is an integer of 0 to 2; and i) R⁴is selected from the group consisting of deuterium, halogen, a C₆-C₆₀aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing atleast one heteroatom of O, N, S, Si, and P, a halogen group, a C₁-C₅₀alkyl group, a fused ring group of a C₆-C₆₀ aromatic group and a C₃-C₆₀aliphatic group, a C₂-C₂₀ alkenyl group, a C₁-C₃₀ alkoxy group, and aC₆-C₃₀ aryloxy group, or ii) in the presence of a plurality of R⁴'s, theplurality of R⁴'s each are different from or the same as each other andadjacent R²'s may be linked to each other to form at least one ring(provided that R⁴ forming no ring are the same as defined in i) above).4. The compound of claim 1, wherein the compound is represented by oneof the formulas below:

wherein in Formulas 6 to 9, X¹ to X⁸, Ar¹, Ar², L¹, and L² are the sameas X¹ to X⁸, Ar¹, Ar², L¹, and L² defined in Formula 1 above.
 5. Thecompound of claim 1, wherein the compound is one of the compounds below.


6. An organic electronic element comprising: a first electrode; a secondelectrode; and an organic material layer positioned between the firstelectrode and the second electrode, wherein the organic material layercontains a compound of claim
 1. 7. The organic electronic element ofclaim 6, wherein the organic material layer contains a mixture of two ormore compounds according to claim
 1. 8. The organic electronic elementof claim 6, further comprising a light efficiency improving layer formedon at least one of one surface of the first electrode and one of thesecond electrode, which is opposite to the organic material layer. 9.The organic electronic element of claim 6, wherein the organic materiallayer is formed by a spin coating process, a nozzle printing process, aninkjet printing process, a slot coating process, a dip coating process,or a roll-to-roll process.
 10. An electronic device comprising: adisplay device comprising the organic electronic element of claim 6; anda controller driving the display device.
 11. The electronic device ofclaim 10, wherein the organic electric element is one of an organiclight emitting diode, an organic solar cell, an organic photo conductor,an organic transistor, and an element for a monochromatic or whiteillumination.